Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Effortless And Fab Rhinestone Strappy Flat Sandals
These faux leather flat sandals are your ticket for looking effortless and fab out with friends! Designed with a chic square toe and a mix of rhinestone embellished and plain straps, these sandals will add a touch of glamour to any outfit. Plus, their easy slip-on-and-off design makes them perfect for switching out heels or styling on the go. Complete the look with a cute handbag.
Fit & Features
- Flat sole
- Slip-on
- Strappy design
- Square toe
- Luxe fit cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1151
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Factor Ruched Velvet Burnout Mini Dress
Level up the luxe factor of your going-out look with this chic velvet burnout mini dress! The lined mesh fabric is accented with an intricate velvet burnout scroll pattern for that eye-catching vibe. The mini-length dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams to accentuate your curves, and a bodycon silhouette. Style with lace-up stilettos!
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Velvet burnout scroll pattern
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5521
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ever So Charmed Puff Sleeve Floral Babydoll Dress
Everyone will be charmed by you in this adorable floral babydoll dress at parties and afternoon soirees! Crafted from an airy woven fabric showcasing a floral embroidered pattern, this short dress will be your staple for spring to summer. Features trendy puff short sleeves, a flattering square neckline, and a babydoll silhouette with a short-length hem. Complete the look with heeled sandals and a fab ring set.
Fit & Features
- Airy woven fabric lined with woven fabric
- Floral embroidered pattern
- Stretchy smocked back, zipper and hook-eye closure
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05101-3358
Category Name: Vacation Looks
Price: $10.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset View Satin Abstract Mesh Corset Top
The perfect abstract satin corset top for dinner with a sunset view! Featuring a sweetheart neckline, adjustable spaghetti straps, and molded cups for support. The sheer mesh bodice offers a snatched look with flexible boning inserts while the cropped hem flaunts your figure and multiple back hook and eye fasteners allow for a customizable fit. Complete the look in form-hugging shorts for a sexy style!
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Built-in padded underwire bust
- Sheer mesh bodice, flexible boning, cropped hem
- Multiple back hook and eye fasteners
- Abstract print, satin fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06001-5015
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Daze Tie Front Mesh Crop Top
Elevate your beachside days in this tropical mesh crop top for layering over your swimsuit or bandeau! Designed with trendy long flare sleeves that create an eye-catching look, this must-have top features a flattering tie front detail that accentuates your figure along the crop hem.
Fit & Features
- Tropical print, sheer mesh fabric
- Long flare sleeves
- Tie front design, open front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-000008
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Rhinestone Criss-Cross Strap Faux Leather Sandals
Amp up your warm-weather 'fits with these glam rhinestone strappy sandals! Made with a smooth faux leather material, these sandals feature a square-shaped toe with a curved criss-cross strap design accented with mini rhinestone embellishments for that chic sparkle. The slip-on-and-off design on the flat sole allows for effortless styling, and the lightly padded insole provides comfortable wear. Pair these sandals with hoop earrings.
Fit & Features
- Flat sole
- Faux leather upper
- Square toe
- Curved criss-cross strap design, mini rhinestones
- Slip-on-and-off styling
- Lightly padded insole
- Runs true to size
Style Number/Barcode: 07404-1173
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine Chic Espadrille Wedges
Take a chic stroll in this espadrille wedges on a sunny day perfect for giving every outfit a fresh lift! From beach days to pool parties, and vacay, these wedge sandals are a must to have in your lineup. Designed with an almond toe, a wide strap for comfort and support, and an elevated wedge heel with a rubber sole. Complete the look with a jelly handbag to keep your essentials in!
Fit & Features
- 4" Wedge heel
- Slip-on
- Almond toe
- Faux leather footbed, rubber sole
- Espadrille material
Style Number/Barcode: 07406-0349
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Bound Tropical Print Woven Maxi Dress
Jet set to your gorgeous getaway in this tropical woven maxi dress! The lightweight gauze woven fabric features a bold tropical print to bring the allure to your dreamy vacay. The maxi-length dress is shaped with a strapless straight-across neckline with a ruffled fold-over design to add a flirty flair. The fitted high waist seam has an elasticized design for added stretch and a thin tie-front belt with cute tassel accents. The dress flows out to a floor-length hem with an effortless A-line silhouette. Style this maxi dress with strappy sandals.
Fit & Features
- Tropical printed gauze woven fabric with short knit lining, minimal stretch
- Strapless straight neckline with no-slip strip, ruffled fold-over design
- Fitted elasticized high waist seam
- Tie-front belt with tassels
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5678
Category Name: Vacation Looks
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adoring Looks Puff Sleeve Lace-Up Peplum Crop Top
Catch many adoring looks in this peplum crop top perfect for your upcoming weekend plans! With a flattering elasticized square neckline, adorable short puff sleeves, and a peplum hem, this crop top is both flirty and cute. The lace-up back adds a touch of unique flair to the woven fabric. Style this crop top with a denim mini skirt and sandals.
Fit & Features
- Woven fabric, no stretch
- Lace-up
- Peplum crop hem
- Runs true to size
Style Number/Barcode: 06003-2443
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten Me Up Square Neck Cutout A-Line Midi Dress
Sweeten your style in this breezy A-line midi dress perfect for bridal showers, day dates, or brunch! With a sleeveless square neckline and adjustable spaghetti straps, this cotton midi dress offers a flattering fit while the stretchy smocked bust with lace-up detail adds a touch of sweetness. The cutout back with elasticized straps adds a hint of daring to the fitted bodice and A-line silhouette. Complete the look in strappy sandals for a chic allure.
Fit & Features
- Lightweight cotton woven fabric with lining
- Adjustable spaghetti straps
- Smocked lace-up bust
- Cutout back
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5611
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clearly Adorable Tote Bag And Pouch
So adorable, this clear tote bag and pouch will be the cutest addition to your closet! The large clear PVC tote is accented with a sleek faux leather trim, faux leather shoulder straps, and an attached faux leather pouch to keep all of your essentials on hand. Style this trendy tote with rhinestone stud earrings.
Fit & Features
- Large clear PVC tote design
- Faux leather trim
- Dual faux leather shoulder straps
- Faux leather zipper pouch
- Lobster clasp detail
Style Number/Barcode: 07203-1934
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Attraction Toe Ring Strappy Block Heels
A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look!
Fit & Features
- 2.5" Block heel
- Square toe
- Strappy design
- Toe ring trim
- Luxe fit cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-5260
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Up Gemstone Strap Jelly Sandals
Glam up your look for spring and summer with these fab gemstone strap jelly sandals! Made from a trendy jelly material, these sandals feature a round toe, a mini rhinestone-embellished trim, and a thin thong strap design accented with iridescent gemstones and rhinestones for that gorg sparkle. The slip-on-and-off design on the flat sole allows for effortless styling. Pair these sandals with rhinestone fringe earrings for even more glitz!
Fit & Features
- Flat textured sole
- Jelly material
- Round toe
- Thong strap design
- Iridescent gemstones, mini rhinestones
- Slip-on-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1177
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance Me High-Rise Hanky Lace Midi Skirt
Bring the romance to your style in this lace midi skirt - a chic option for birthday dinners or parties! The high-rise waist and slim-fit silhouette flatters your figure, while the flowy hanky uneven midi-length hem adds a playful touch. Made with delicate floral lace fabric with a knit lining, this skirt exudes elegance and charm. Complete the look in a corset top and block heels.
Fit & Features
- Sheer floral lace fabric lined with stretchy knit
- High waist
- Mid-length flowy hanky hem
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 06501-1019
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Irresistible Floral Lace Corset Mini Dress
You'll be simply irresistible with your gorgeous allure in this floral lace corset mini dress. Airy and sheer, the lace fabric is accented with a romantic floral print and includes a partial knit lining for coverage. The mini-length dress is shaped with a feminine sweetheart neckline with a padded bust, and adjustable spaghetti straps for that customized fit. The corset-style bodice features sheer inserts for a hint of skin and has flexible boning for a snatched silhouette. The bodycon fit will flaunt your stunning curves. Complete your date night look with the perfect pair of heels!
Fit & Features
- Floral printed sheer lace fabric with knit lining, moderate stretch
- Sleeveless sweetheart neckline with padded bust
- Adjustable spaghetti straps
- Corset bodice, sheer inserts with flexible boning, high waist seam
- Back zipper with hook and eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3138
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slip Into Luxury Rhinestone Flat Jelly Sandals
Slip into luxury with these jelly sandals on vacation or a weekend spent under the sun! Featuring a sparkling rhinestone band and a comfortable square toe, these slide sandals will add a touch of glamour to any outfit. Made with soft and durable jelly material, they are perfect for slipping on and off. Complete the look with trendy sunglasses.
Fit & Features
- Flat sole
- Jelly material
- Rhinestone embellished strap
- Square toe
- Runs a half-size small, recommend sizing up
Style Number/Barcode: 07404-1186
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Sheen Metallic Woven Faux Leather Sandals
Step out and shine with a glamorous sheen in these metallic woven faux leather sandals! Made with a sleek faux leather material with a glitzy metallic sheen, these sandals feature a square-shaped toe with a wide strap with a trendy abstract woven design. The slip-on-and-off design on the flat sole allows for effortless styling, and the lightly padded insole provides comfortable wear. Pair these sandals with a mini tote bag.
Fit & Features
- Flat sole
- Faux leather upper, metallic sheen
- Square toe
- Wide strap with woven design
- Slip-on-and-off styling
- Lightly padded insole
- Runs true to size
Style Number/Barcode: 07404-1172
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Tropical Print Flowy Maxi Dress
This tropical print flowy maxi dress is giving major weekend getaway energy! The breezy lightweight woven fabric is detailed with a tropical leaf-outlined print, perf for your next vacay. The maxi-length dress features a sleeveless square neckline and adjustable spaghetti straps for a customized fit. The high waist leads to a cute tie-back design, followed by a lower back cutout for a hint of skin. The dress flows out in an A-line silhouette with a stylish tiered design. Complete your look with gold hoops and strappy sandals.
Fit & Features
- Tropical printed woven fabric
- Sleeveless square neckline
- Adjustable spaghetti straps
- High waist with tie-back design, lower back cutout
- Flowy A-line fit with a tiered design
- Runs true to size
Style Number/Barcode: 05102-5609
Category Name: Vacation Looks
Price: $21.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Attention Getter Strapless Newspaper Print Mini Dress
Capture attention with all eyes on you in this fab newspaper print mini dress! The textured lined woven fabric features a newspaper print with rose print accents for that trendy-girl vibe. The strapless straight-across neckline is detailed with an eyelet lace and thin velvet ribbon trim, tying at the center. The bodice features a bust seam outline with ruching to accentuate your figure. The flexible side boning adds structure, while the hidden back zipper offers effortless styling. The form-hugging fit on the mini-length hem will flaunt your stunning curves. Style with a layered choker necklace.
Fit & Features
- Non-stretch textured lined woven fabric, rose newspaper print
- Strapless straight neckline with no-slip strip
- Eyelet lace and velvet ribbon trim, tie-front, bust seam outline with ruching
- Flexible side boning, hidden back zipper with hook and eye closure
- Form-hugging fit
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05102-5644
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Glitz Rhinestone Strap Faux Leather Sandals
Add a glitzy shine to your casual looks with these glam rhinestone strap sandals! Made with faux leather material, these sandals feature an open round toe, followed by a wide banded strap embellished with sparkling mini rhinestones. More rhinestones outline the flat sole. The open back offers effortless on-and-off styling. Pair these sandals with a choker necklace!
Fit & Features
- Faux leather material
- Open round toe
- Wide banded strap
- Rhinestone embellishments
- Open back, flat sole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1187
Category Name: Vacation Looks
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Topic Strapless Denim Midi Dress
You'll be the topic of conversation in this denim midi dress for the trendiest look at casual hangs or brunch! This stunning denim dress features a strapless neckline and a form-hugging silhouette that will accentuate your curves. The belt loop accents and four-pocket styling add cute functional details, while the front center slit and midi-length hem provide a modern touch. Complete the look in sleek hoop earrings and pumps!
Fit & Features
- Denim fabric with minimal stretch
- Belt loops, four-pocket styling
- Front center slit
- Side zipper closure
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5455
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Sleek Square-Shaped Sunglasses
Simply sleek and chic, these square-shaped sunglasses will level up your looks. They feature a small square-shaped design with tinted lenses, a thin metal frame with thin arms, a thin nose bridge, and rubber nose pads for support. Style with small hoop earrings for that trendy girl vibe!
Fit & Features
- Small square-shaped design
- Tinted lenses
- Thin metal frame and arms
- Thin nose bridge
- Rubber nose pads
Style Number/Barcode: 07008-1047
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Loved In Lace V-Neck Long Sleeve Short Dress
A divine lace short dress for modern brides, birthday babes, or any dressy occasion! The mini dress features sheer lace long sleeves with flared cuffs, a V-neckline, a bodycon silhouette that hugs your curves and is composed of a lace knit fabric with stretchy knit lining. Complete the look with fringe earrings and heels.
Fit & Features
- Sheer long sleeves, flared cuffs
- V-neckline
- Bodycon silhouette
- Short-length hem
- Lace knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3171
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Staple Square-Frame Sunglasses
These sleek and chic square-frame sunglasses will be a staple for the season! A trendy take on a classic design, these shades feature a square shape with a subtle angle, tinted lenses, a plastic frame, and mini-studded accents on each side. Style with hoop earrings.
Fit & Features
- Square-shaped design
- Tinted lenses
- Plastic frame and arms
- Studded accents
- Built-in nose pads
Style Number/Barcode: 07008-1049
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free